


10 Dollars

by hellhoundsprey



Category: Supernatural
Genre: Crossdressing, Feminization, M/M, Masturbation, Mutual Pining
Language: English
Status: Completed
Published: 2015-10-09
Updated: 2015-10-09
Packaged: 2018-04-25 14:15:38
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,053
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4963825
Author URL: https://archiveofourown.org/users/hellhoundsprey/pseuds/hellhoundsprey
Summary: <blockquote class="userstuff">
              <p>Dean takes his little brother to a carnival.</p>
            </blockquote>





	10 Dollars

**Author's Note:**

> No ages specified.

A stone's throw away from Milwaukee, I am eating dinner with you. Dad left this morning and you're babbling about your day at school as if I hadn't been with you half of recess and the entire lunch break. Your food bores you, so you paint circles into it with your spoon while you talk to me with a lonesome splash of tomato sauce in the corner of your mouth. I watch it being swiped away by your candy-pink tongue after I say, "Eat up, Sammy, c'mon."

You don't know yet, because I kept it secret - I know you love surprises. The anticipation was all worth it when I finally tell you over the dishes that we're going out tonight, just you 'n me, baby boy, and your expression explodes from sulky to a million dollars. I only saved up ten but I will pay you back eventually, promise.

There are booths with food and activities lined up along the bay. We saw it when we drove through town together with Dad. You hadn't dared to exclaim how bad you wanted to go there but you can count on me to always notice your desires in those big, gleaming eyes.

"I want you to wear this," I say. I hand it over to you.

Your hands are tiny. The light pink fabric looks so out of place, so stunning against your tanned summer skin. You stare down at it, up at me. Pink creeps into your cheeks. I know mine are alit already.

"So we can play pretend," I explain in a low voice. Nobody hears us but the words feel too precious to be spoken out loud and dirty. "Me an' my baby girl on a sweet lil' date."

Your shaggy hair falls into your eyes as you look back down. We both know you're not looking for a way to say "no" but for a way to not yell "thanks" and break into tears. I know it's hard on you. You deserve someone you can hold hands with in public without being afraid to be seen. But you chose me. Out of them all, you chose me.

"Okay," you mutter, and off you are into the bathroom. While I listen to the lock being turned, I drop down on one of the beds, put my elbows on my knees, wipe my face with both hands. We're fucked up, fucked up right down to the roots. I only handed you the damn thing, told you we were going to a carnival together, and I'm already hard enough to pound nails. You are the best thing in my entire life and all I want to do is walk the streets together with you without feeling too much like the monster I obviously am. I can wait. I can wait for a lifetime and longer, and if you're never ready, I'll never be sad about it. Just stupid little things like this bring me to the edge of tears. That's what you do to me.

You come back out and I decide to look into your flushed little face instead of at the way the pleads of the skirt fall around your tiny hip, the too-big boy tee you didn't bother to change out of (and you're right, it goes amazingly well with the skirt), your bare thighs, the bruised mess of your knobby knees. You're wearing the least destroyed socks you could find together with your regular sneakers. I don't have to tell you how beautiful you are for you to know it. I get up, hold my hand out for you to grab it. You do. "Alright, let's go."

Our hands are slick and warm in the summer heat, even after nightfall. Yours is so tiny in mine, but it used to be even smaller when all this started. You're growing so much lately. I can't wait to let you wear even more of my shirts.

We're both shaking a bit even though nobody here knows us. They don't know that we're siblings, don't even know you're a boy as long as they don't stare too closely (and nobody does). We're a regular couple, young, maybe, but for a girl your height promises an appropriate age to go along with mine. You're a slim, shy girl with wild hair and no tits, and I'm your slightly swelled, broader boyfriend. That's who we are tonight, and I know you love it just as much as I do. We're ticking in the same way in that department, you and me.

By the time we reach the bay, everything's a bit calmed down inside of us. You nod when I throw you a questioning "ready?" look, and you almost don't pinch your lips together. So we fit ourselves in between the crowd.

We just ate but I know your stomach runs extra hours lately. And you're still a kid and this is _candy_. Even though I love candy just as much (and maybe even more than you), my ten dollars will be spent on you and you alone. Your mouth gapes at the sight of shiny-red candy apples, so I get you one for two bills. It crunches between your teeth, both apple and sugar, and your young mouth is too unskilled to keep the sweet juice from pouring down your chin. Your arm is hooked in mine and we pull each other along. "Good?" I ask, and you smile at me with tinted lips, kid-mouth on too many varieties of sugar, and you let me have a bite of your treat. I chase your spit where you took a bite and moan into the apple.

Roasted almonds, three dollars. We share it because you insist. Your tiny fingers pop the candy between my lips and you lick them without thinking about it once you've finished off the bag. "I'm so full!" you huff, rub your tiny little tummy that wouldn't show under your shirt even if you tried. I say, "Lemme see," and you let me place my palm where you just touched yourself. Your body burns hotwarmlovelyfull underneath my skin, underneath worn cotton. Your skin pulled taut, you were right, but I can talk you into cotton candy five minutes later. Your tongue chases baby-pink sugar, not much different compared to your skirt, so much lighter than your tongue or your lips or your cheeks. You are so much darker, so much more tainted. I watch you.

Four dollars left now. The Ferris wheel comes in sight as we proceed down the bay. People are starting to go home. It's about ten PM.

You point at the blinking lights of it, and you chase my eyes down before you say, "Can we go on that one?"

I smile and am in love with you and I say, "'Course, baby."

One-fifty each. One dollar left. We have the booth to ourselves and your skirt jumps over your thighs when you let yourself plop down right next to me. Even through my jeans, your skin lights me on fire. You get the window seat (of course) and I hear you gasp over the beauty of Lake Michigan at night. We hold hands between our legs, on top of them. I watch the colorful mirrors of the lamps flicker on top of the black water together with you and I try to sell you a cheap horror story about mutated mermaids who are attracted by the carnival's annual lights. You snort, not even laugh but _snort_ , because you are very clever and you know me, but you smile sweetly and frown as if you wanted to say that I was adorable. Then you say it out loud and dig your elbow into my ribs. I laugh and lean on to you while we rise higher and higher.

We watch the water, hold hands. You smell like candy and soap and little boy and big boy. I nuzzle your hair because it's so soft against my face, because my breath tickles you when I put it here. You make a noise between pleased and annoyed and you squeeze my hand tighter in your own.

Into the silence of our booth, you whisper, "I think I'm starting to grow hair," and I feel my heart ache even before you add, "Down there," as if I didn't understand that right away.

My exhale comes shaky and I can't help but smile over the shy eyes, the pouty lips. You think I'm making fun of you when I just try not to lose myself. "Wow," I hear myself say. I don't have words for what I'm feeling.

You crane your neck but my cheek is too far away for you to peck a kiss at. I am not dumb. Your breath smells like everything I could ask for. "Can I show you?"

My laughter feels bitter and too light-headed, and I am stupid for it because I know it makes you feel horrible. You don't want to be treated like the kid that you are so so badly, and I know, baby, I know. But even stubble wouldn't turn you into any more of an adult as you are right now. I know you're hurt and that you're miserable, so I chuckle and say, "Yeah, okay."

I expect you to pull back the hem of your skirt and underwear like you would do if you were wearing jeans right now. Instead, you let go of my hand and lift up your skirt.

You're naked underneath, paler than everywhere else and as hairless as ever, little dick standing up proud and as tall as it will get. I slam my eyes shut and turn my face away.

"You didn't even _look_!" you protest, voice shaking and hurt, and I assure you that yeah, I indeed saw enough, but you won't have that.

You know that I only do what is best for you. You know that I don't want to do anything that could possibly hurt you. You know I think you're too young to do all those things you keep asking about, and goddamn, you know what your puppy eyes do to me.

"Okay," I breathe, "Alright, I'll look." I sneak my hand back into yours, peel my eyes open for a little slit that lets me see your lap in the darkness. There's a tiny wet spot where your dick must have poked against the skirt.

You hold your dick down with your free hand, run your thumb over the skin above it. "Here," you explain. I don't see anything, but I nod. Your hand roams deeper, lifts your sack. "An' here." You sound nervous.

I hate it when you put yourself through things like that. I told you I wasn't seeing any girls. You know I'd have to rip myself into actual pieces to give my attention to anyone but you. You don't have to prove anything to me. You _have_ me. I can wait. I'm not mad about waiting.

Your eyes are a little wet when they look back up into mine. We're almost on top of the wheel and my little brother is showing me his genitals with his skirt flipped up to his stomach full of candy. I swallow, sigh.

My free hand brushes your leg, puts itself down on your knee. The thought of a pull goes through me, but I push it away. "A little wider," I whisper. "Lemme see properly." I am going to hell.

You comply without the second of hesitation, of course you do. Your legs go for miles and the gap between them could fit two of me. I won't touch. You know I won't touch, and maybe that's why you're trying to make me see so much more than I can handle. I bury my face in your nape of the neck, and it's damp here with little boy sweat, and I can hear your heart because it's so so big in your so tiny body, and I close my eyes because I can't take it. It horrifies me every time just how much you are willing to give, how deep your trust for me runs. It's what keeps me going, though, because it reminds me that I could never ever misuse any of it.

"I don't see no hair." I run my knuckles over your leg that presses against mine. "Soon though, I'm sure. Jus' a little more time, buddy." You shake under my chin. I know, baby, I know. On top of the Ferris wheel, I make you flip your pretty little skirt back in place.

On the ground again, I feel more unstable than on the damn thing. You hold my hand, nudge my shoulder. I feel your hand on my cheek and you must stand on the tip of your toes but you're reaching my mouth to kiss it. I repeat to my screaming brain that it's okay, that we're playing pretend, that nobody knows, but I feel eyes on us and hope you aren't flashing anything. The thought makes my dick throb. You rock back on your heels after you're done with me, cheeks still pink, and you press up against me because your dick is still tenting the skirt a little. We manage to walk like this until you're soft again. Mine hasn't gone down ever since it went up back in our tiny little apartment. It is neatly tucked away between seam of jeans and underwear. Precautions are my department.

One last dollar, and I spend it on candy corns just as colorful as the Ferris wheel's lights. They press against the insides of your cheeks and I can imagine your tongue swirling around them, and you don't even mean it in a sexual way this time and that's what hurts me the most. I lean down and kiss you in front of all people, cradle your face in front of all people, allow my tongue to peek between your lips and into the sugary cave of your mouth in front of all people. I feel you sigh and tense up, melt under me, because I have this power that no one else has over you, and I love it.

We part and you whine, press up close against my hip again. I put my arm around your still narrow shoulders and guide you away from the people, the lights, the carnival. You eat your candy and I try to calm down my heartbeat.

It's not the way that leads back home. When you notice, you ask me where we are going. Without looking at you, I raise your hand that still is entwined with mine and kiss your already too-rough knuckles. You don't ask any more questions after that.

In the darkness, everything seems to be easier. I almost can't see my hands, my feet, can only feel your warm skin against mine, your heart drumming your ribs open like a birdcage's gate where it's pressed against my arm. A deserted park, midnight, shadows under heavy, green trees. I place you with your back to one of the oaks, loom over you the way I know you like it, and I kiss you, here, where nobody can see.

My hands slide over your shoulders. They get broader every day, every second. If I had a camera, I would document every single inch. "Where'd your boxers go?" I whisper.

"They peeked out underneath," you mutter. You sound so young when you whisper. "'N all my briefs were in the laundry." Your fingers splay over my chest, side-to-side around the necklace you gave to me. You look at it, up at me. "Are you mad now?"

I chuckle, bow closer, nuzzle your neck. "'Course not. Jus' didn't, uh, expect it, ya know. You goin' commando like that. For a date, out of all times."

"Does. Does 'commando' mean 'no underwear'?"

"Yeah."

"Oh, okay."

"You're too sweet for me, Sammy."

You shake your head and I kiss your neck.

"Yeah," I groan, "Yeah, you are."

"No," you whimper. You drop your candy to the ground to paw at my dick, without any idea about how to do it, without any finesse. It almost has me creaming my jeans.

I recoil from your hand and you make an impatient sound. "No," _I_ say this time.

" _Please_." Because I won't let you touch my dick, you have tears in your eyes. This is how far it has come with us, how far I can drag you. "Please, jus' a little. I promise I'll do it right."

That's not the point and you know that. "We talked about this," I remind under a smile, hold your little wrists as if they were twigs that I could break with a snap of my fingers. I watch how the front of your skirt turns a little dark where you're making it sticky-wet. "We should go home."

"No!" You're legitimately crying now. You're too old for this kind of behavior. You only let this out when we're alone, just like you try to convince me that you're old enough to fuck by letting me inspect your peach fuzz only when we're alone.

I love how much you love me and how much you need me. But you don't understand these things yet, and even though I'm just as far away from being an adult as you are, I have to be responsible for both of us. "C'mon, Sammy. Need to get you into bed. It's really late."

You wail. Yeah. I don't want this to be over either, but we have no choice.

I kiss your neck for a last time. I don't suck hickeys in it or bite it. We have no alibi for that yet. "We'll get you out of that skirt, sweetheart, alright? Back home?"

Crying turns into sniffling rather quick. I watch your dick squirm underneath the pink fabric before I let you go. "Okay," you say eventually.

"Okay," I repeat under a nod. When I bend down to pick up your sweets, I avoid looking at your crotch where you're trying to hide the now outstanding spot.

We walk home in pitch blackness, both unable to calm our thoughts, our bodies. I try to calculate just how far we can go tonight, maybe just a little, maybe just the fragment of another inch. You were really good tonight and we have this unspoken rule that when you do what I tell you to do, you get a reward. It's fucked up, I know, and it's starting to get a little out of hand, but I can't help it, somehow. I want to spoil you rotten.

Back in our apartment, I re-set the salt line. When I turn back around, you're standing there like sin itself. Hands behind your back, cheek fat with another piece of candy. You took off your socks and sneakers and bathe your blackened toenail in the light that falls through the broken blinds.

I look at you for a moment, soak in the warmth of your gaze, the hotness of your cheeks and tips of ears. "My pretty girl," I breathe.

You cradle my head as I go down on my knees in front of you, hear your soft gasp. I slip away from underneath them though, run my mouth down your smooth thigh where it's so toned for a little boy that it shouldn't be possible, slim and compact and so so different from any girl's I've ever had. You're better than any other girl there is. I didn't know I could want something that didn't have a pussy but it was the most natural thing to me when I realized that it was you who I wanted. It just came with the fact, I guess. Your knee tastes salty in between my teeth. You jump a little. Your fingers fly over the very tips of my hair.

I bow down to the ground, kiss your shins, ankles, feet, toes. I love every inch of you. I crane my neck on the way up, arch my back for you to see what kinds of animals I can be for you. My teeth get a hold of the hem of your tiny skirt. I pull it down just to let it swing up again, to make your dick jump with it. You whimper from something as easy as that.

You smell so good. I didn't know jizz and balls and boy-sweat could smell this wonderful, that I would ever start drooling from only thinking about what you taste like. But here we are.

"You got it all dirty," I groan against that spot. I lap at it.

You startle, hard, and your hands are back in my hair, both of them. I hear the candy click against your pretty teeth, hear your breath starting to rattle. I lap again and taste salt, shudder. I wonder if all that candy will show in your taste down here in a few hours.

"Bed," I say.

You're on it in the blink of an eye, hair wild where you're pressing your head into a pillow, tee riding high on your tummy, skirt flipped over, hands on your dick in between spread-apart legs. I climb next to you while I unzip my jeans, yank out my dick. We don't touch each other, but we touch ourselves next to each other. It's my rule, and I'm not breaking it. For now. I'm thinking about changing it on your next birthday, but I think I'll have to decide once the time comes, when I know how far you are at that point. I measure you on things you don't understand.

I lay down and watch you watching me. You stare at my dick in my hand like it's a work of art, as if you've never seen it before. It's not that impressive, actually, but for you it must look like... I don't even know. I don't know what you're thinking about when you're staring at my dick like you wanted to eat it. Even if you were brave enough to do so, I'd probably wouldn't let you say any of it out loud.

We kiss and share your candy in between our tongues. Your breath hitches. You're always coming quick when we're doing this together. You told me you were making progress with holding it, but I have my doubts about that. The candy dances between the tips of our tongues and finally slips back into your mouth when you lose control over your body. You moan that tiny, almost broken sound that echoes through the dusty room, through my ears and my head and my bones. My fist is going violent now and I don't need too many drags with your writhing body so close to mine to reach my limits as well.

I turn to my side, squint down your body, find the spot where you left a sorry little puddle and turn it wider, whiter. You didn't expect it and moan again, don't let go of your barely-handful of dick, watch mine splatter skirt and skin. I rub the mess in with the head of my dick, rub off against your belly full of cotton candy and sugary apple and tomato sauce. I pant into your hair and taste your sweat on the back of my throat. We watch my come pearl out of that tiny slit together, how your pink skirt eats it up. You lift it a little for the thick white to pool in your belly button. It's too small to fit it all and everything drools out and over your skin, down your belly, the barely-there cave of your hip bones. I sigh, and you sigh because I sigh. We're both tired and both don't want to end this day, but in the end, we'll have to give up.

You crane your neck, kiss me, breathless and slow, with too much spit. I chew on your lip just because it makes you make that dirty sound, something only I can make you do. The candy wanders into my mouth and I lazily roll my tongue over it. It tastes like everything that is wrong about us and everything that is right about you. It was worth every penny.


End file.
